Triethylamine → 2-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid

HRID 871874

反応式

HRID 871874 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[NH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15].C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][CH2:13][C:14]([OH:16])([CH3:17])[CH3:15])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 951022-Propanol, 1-amino-2-methyl-HCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acid

生成物 1

HCID 866731432-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid収率 59.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
3.5 °C

実験手順

A suspension of 19.9 g (86.73 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid in 155 mL of THF is cooled on an ice bath to 2-5°C., and a solution of 8.5 g (95.40 mmol) of 1-amino-2-methyl-2-propanol and 36.3 mL (260.19 mmol) of triethylamine in 60 mL of THF is added dropwise. The mixture is stirred at room temperature overnight. Ethyl acetate and water are added. After separation of the phases by settling, the aqueous phase is acidified with aqueous 1N HCl solution to pH 2. The precipitate is isolated by filtration to give 12.6 g of the expected product in the form of a pale yellow solid, which is used as obtained in the following step. Yield=59%.

後処理

  1. customAfter separation of the phases
  2. customThe precipitate is isolated by filtration

出典と根拠

ORDレコード
ord-f1b8463a504b4795b4911c5acf111e44
出典データセット
uspto-grants-2015_03
特許番号
US08975250B2

関連ノート

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